George Clooney and Sydney Pollack in Michael Clayton. Myles Aronowitz/Courtesy of Warner Bros.

Because it was rumored that George was interested in directing it?
Sydney Pollack got involved because Sydney wanted to direct it. I said: "I'm sorry." And then I met him, and he said: "Well, all right. I'll help you make it." And then along the way, [producer] Steven [Samuels] read it and — because we were working together — and he sent it to George. And George came back and said: "Hey, I really like this. I might want to direct it. But I don't want to meet this guy, and I don't want to work with a first-time director." That was almost two years later before we finally met. [Later], we had this like marathon 11-hour meeting at his house when I finally got to meet him.

And where you connected over your love of the same movies?
Everything. Yeah. We had a lot of points of connection. It was just a really comfortable all-day conversation. It was just a really good meeting.

Was it intimidating being in the situation where you have two lead actors who are both very accomplished directors? Did you struggle to convince Sydney Pollack to act in the film as opposed to direct it?
To be an actor? Yeah, to show up, I did. It was a complete pain in the ass to try to get him to show up! He kept trying to back out. Because he's really busy and then he was nervous about acting in a film that he was producing. I was like: "Sydney, you would be in this part no matter what. Even if I'd never met you, I'd be bugging you to be in the movie." Because he's just the perfect casting. So, it was a real struggle to get Sydney to be in the movie. When he finally showed up, it was fine. But I really had to keep pushing him all the way down the line. Well, the most important part is I needed someone who would intimidate George. I needed an actor who would have authority over him. That's not an easy thing to find. That's often a problem you find. You really want to have two actors in the scene, and they're supposed to have equal weight in the scene and you got a movie star and somebody else. It's really hard for the audience to not carry forward the gravity that they've attributed to those people. So I really needed somebody who really could keep George on his ass.

Shooting in New York, how did you get into those law firms? Were they aware of what the film was really about?
Oh, man, that's a good question. Yeah. That was the most unanticipated and difficult part of the whole picture — because we didn't have any money to make this movie really.

The budget was around $17 million?
Yeah. But 45 days in New York City, and we can't buy locations with very limited funds. The days shooting in New York were very expensive. And finding those locations was just critical — hanging onto them once we found them, too. And so we really had to make it a positive experience for the law firms. It's interesting. Lawyers don't perceive this movie as being anti-lawyer at all. And I don't perceive the movie that way. So lawyers look at the script, see the movie and go: "Well yeah, that's real. I recognize that and those are the kind of compromises." But there's nothing evil that the law firm itself does. The malignancy there is cultural — not what they do. So they don't see it that way. So there was no problem sort of vetting the script. The real problem is: "Can we bring 80 people in and disrupt your law firm for four or five days?" And there's a law firm in New York called Dewey Ballantine. I had a personal connection through a friend, and we just went in and begged them. We also were really diligent about how we treated our locations and everybody [there]. So every time we left a place, the next place knew that we were going to leave them in better shape than we found them.